Can I put my $10,000 from my TSA into my shiney new Roth IRA as a "rollover"? I realize that there will be tax consequences, as the money from the TSA is untaxed. Would it be worth coming up with the dollars to pay the tax due on this amount to get it into my Roth? (If this is allowed...)

I like the notion of putting the money into my Roth, as it is in the form of the Vanguard 500 Index Fund....which is Foolish if one wants to use a mutual fund. On the other hand I am thinking that coming up with the taxes on this sum might not make sense.

Boy, this retirement planning stuff is complex, but I had better get going on it as I am definately not getting any younger...